Turbotax isn't going to educate you so unless you'd like to educate yourself and potentially make some costly pitfalls, then I'd outsource.

A formal business built on this seems overkill as you’re essentially paying someone for a service that already has standard model.If you and the parnter have distinct business tasks/abilities (i.e. not what you would hire an agent or contractor for), such as off-market lead generation, that’s a different discussion.

I have had investors pull equity from their homes in the phoenix area to buy cash flowing properties in Fayetteville and similar areas, because the price growth in the phoenix area generates amazing returns.It depends on if you want cashflow now or delayed gratification later.Keep in mind that when you do sell, there are costs to selling and depreciation recapture  and IRS taxes, which eat up most of your "equity" growth. 

I have filled a complaint against him with the Better Business Bureau and the NJ State Attorney General. 

Only reason I've been doing it is to get 0% business credit card limit increases.  

By the end of 2 years, I could save 50-60k for a down payment, closing costs, and reserves. 

Tenant shall be charged $[amount] to cover the cost of this force-placed insurance.The other lesson is that you should never hand over keys until you have proof the Tenant has met all requirements.

You can also gain valuable experience virtually and offer low or no cost "co-hosting" services.

Are the business on there trusted? 

Evaluate Property ConditionOlder Chicago buildings often have charm—but may come with hidden costs.